Additive-releasing filter for releasing additives into tobacco smoke



United States Patent 3,280,823 ADDITIVE-RELEASING FILTER FOR RELEASINGADDITIVES INTO TOBACCO SMOKE Abraham Bavley, Bon Air, and Ernest W. RobbII, Richmond, Va., assignors to Phiiip Morris Incorporated,

New York, N.Y., a corporation of Virginia No Drawing. Filed Oct. 1,1963, Ser. No. 312,879 1 Claim. (Cl. 131-10) This invention relates toan additive-releasing filter for tobacco smoke for releasing additivesinto tobacco smoke. More particularly, the present invention relates toan additive-releasing filter for tobacco smoke for releasing additivesinto tobacco smoke, which additives can be maintained and preservedduring storage of the tobacco products containing them and whichadditives are released in controlled amounts when tobacco smoke passesthrough said filter.

One of the additives which can be released into tobacco smoke inaccordance with the present invention is nicotine. It has long beenknown in the tobacco industry that in order to provide a satisfyingsmoke, it is desirable to maintain the nicotine content of tobaccoproducts at a uniform level. However, it is difiicult to accomplish thisresult, since the nicotine content of tobacco varies widely, dependingon the type of tobacco and the conditions under which the tobacco isgrown.

Among the factors affecting the nicotine content of any variety oftobacco are the conditions which exist during the growth of the tobacco,for example, the moisture conditions, the type of soil, the fertilizersthat are employed, the number of tobacco plants per acre and the carewhich is given to the plants during their growth. The nicotine contentalso varies widely, depending on the variety of tobacco. Many of thenewer varieties of tobacco plants yield tobacco which is low innicotine. Furthermore, methods of preparing tobacco products frequentlyremove some or all of the nicotine that is naturally present in thetobacco. In addition, modern technology has made it possible to utilizeportions of the tobacco plant other than the leaves for smoking and someof these portions, such as the petioles, are low in nicotine content.

Maintaining the nicotine content at a sufiiciently high level to providethe desired physiological activity, taste, and odor which this materialimparts to the smoke, without raising the nicotine content to anundesirably high level, can thus be seen to be a significant problem inthe tobacco art. The addition of nicotine to tobacco in such a way thatit remains inert and stable in the tobacco product and yet is releasedin a controlled amount into the smoke aerosol when the tobacco ispyrolyzed is a result which is greatly desired.

Previous efforts to adjust the amount of nicotine in tobacco have notbeen successful. It has not been feasible to add nicotine per se totobacco products. Since it can be absorbed through intact skin, nicotineis difficult and hazardous to handle in processing operations. Inaddition, free nicotine is an unstable material and has been found todecompose readily at room conditions. Thus, if nicotine were simplyadded as the free material to tobacco, it would be likely to decomposeduring storage of the tobacco product, thereby resulting in theformation of undesirable decomposition products and resulting in adecrease in nicotine. Even though the nicotine content of tobaccoproducts could, by the addition of nicotine under conditions involvingconsiderable effort, be made initially uniform, the decompositionattending storage of the product would not provide a smoke containing auniform amount of nicotine.

In copending application Serial No. 149,540 filed November 2, 1961, nowPatent 3,109,436, a solution to this "ice problem has been provided bythe incorporation of nicotine-ion exchange resins in the tobacco. Thepresent invention provides even greater improvements than those attainedin accordance with that invention, in that there are no ion-exchangebreakdown productsintroduced into the smoke.

The present invention provides a solution to this long standing problemand results in accurate control of the amount of nicotine which isreleased in tobacco smoke. By employing the methods and compositions ofthe present invention, it is possible to eliminate the hazards ofhandling nicotine and to incorporate exact amounts of nicotine in atobacco composition which will remain constant over extended periods oftime and which will ultimately yield a smoke containing a controlledamount of nicotine. In addition, the present method does not introduceany ion-exchange breakdown products into the smoke.

Another type of additives which can be released into tobacco smoke inaccordance with this invention is a flavorant. Often flavor or flavorswhich are incorporated in tobacco arellost or altered during subsequentmanuf factoring steps or during storage. Furthermore, it is diflicult tocontrol the amount of flavor released during the smoking of a tobaccoproduct to insure uniformity of tobacco flavor during the entire smokingprocess.

While many efforts have been made to introduce flavors into tobaccosmoke, no completely satisfactory method has been found. For exampleflavoring acids have been incorporated into the tobacco in the form ofstable esters which break down into the acids upon pyrolysis. Such amethod, however, is only useful for certain types of flavorants and alsoresults in the incorporation into the smoke of the other breakdownproducts of the pyrolysis of the esters.

The present invention overcomes the above-mentioned disadvantages. Thisinvention permits the release into tobacco smoke, in controlled amounts,of desirable flavorants, as well as the release, in controlled amountsand when desired, of nicotine into tobacco smoke.

In accordance with this invention, the desired additive is incorporatedin a tobacco-containing article in a manner such that it will not bereleased prior to the time the tobacco product is smoked. By the termtobacco as used in this specification is meant any composition intendedfor human consumption by smoking whethercomposed of tobacco plant partsor substitute materials or both.

The present invention comprises incorporating into a filter for tobaccosmoke a material which can be characterized as an additive-ion exchangeresin. This additive-ion exchange resin may be a flavor-ion exchangeresin or a nicotine-ion exchange resin.

In the case of nicotine, the additive-ion exchange resin can be anicotine-cation ion exchange resin (referred to hereinafter, forconvenience, as a nicotine-cation exchange resin). The resultingcomposition is inert and stable and can be employed in a filter forcigarettes, pipes, cigars, or in other tobacco products. Thenicotine-cation exchange resin will not decompose under ordinary storageconditions and does not impart undesirable odors to the tobacco or thefilter. However, when the tobacco is smoked and the smoke passes throughthe filter, nicotine is released from the nicotine-cation exchange resinand goes into the smoke. The amount of nicotine which is desired in thesmoke can be adjusted within desired limits by the proper control of theamount of nicotinecation exchange resin which is initially incorporatedin the filter.

The nicotine-cation exchange resin, which will hereinafter also bereferred to as the nicotine-resin, can be prepared by contacting acation exchange resin with nicotine under either continuous or batchconditions. When the contacting is done in the batch state, thereactants are agitated in a reaction flask with a volume of resin, whichcan, for example, comprise from to by Weight of the reactant. The amountof materials, the temperature and the time of operation will depend uponthe reactants involved. The mixture is agitated by shaking or stirring.The use of a fine mesh resin will minimize any physical deterioration ofthe resin which might be caused by a stirrer. Particles in the range of100-200 mesh are preferred. At the end of the reaction period, thesolution can be decantered and the suspended resin recovered byfiltration. The resin can then be rinsed and aird-dried and it is thenready for use. The solvent is preferably water, although the other inertliquids in which the nicotine is soluble can also be employed.

Continuous operation in a column can be effected by placing pretreatedresin in a column of suitable size and passing the reactants through thecolumn continuously.

Preferably, the contacting is conducted under continuous conditions.This can be done by packing a column with the ion exchange resin inparticulate form, for example bead form, and passing an aqueous solutionof nicotine through the column. The technique employed can be the sameas .is used in chromatographic columns. As in the case of the batchcontacting, other inert liquids may be employed in place of water. I

In either the batch or continuous method, after the desired amount ofnicotine has been taken up by the resin, the resin can be removed fromthe contacting vessel directly employed in accordance with the presentinvention.

The exact amount of nicotine which is incorporated in the resin can. bedetermined bymethods well known in the art. For example the method setforth by R. B. Griffith in Tobacco Science Volume 1 (1957) on pages130-137 may be be employed. Another method is that described in theOflicial and Tentative Methods of Analysis of the Association ofOfficial Agricultural Chemists, fourth edition, 1935.

The proportion of nicotine in the resin is not critical, so long as theamount of nicotine is known. However, it is advantageous to utilize anicotine-resin in which a considerable amount of nicotine is reacted,since the amount of nicotine-resin required to incorporate anyparticular amount of nicotine which is desired in a filter obviouslydecreases with increasing proportions of nicotine to resin.

A representative equation for the reaction involved in the preparationof the nicotine-cation exchange resin is schematically shown below:

The above equation represents the reaction when the cation exchangeresin is in the hydrogen ion form, as will be described below. A similarreaction could occur with a cation exchange reaction in which thehydrogen ion were replaced with another ion such as sodium ion,potassium ion or other ions. However, the hydrogen ion type ispreferred, because it is more easily replaced by nicotine and morereadily takes up the nicotine upon contact.

Cation exchange resins which may be employed in accordance with thepresent invention may be strong cation type resins, intermediate cationtype resins or weak cation type resins and can, for example, be any ofthe commercially available cation exchange resins.

Satisfactory strong cation exchange resins include the sulfonic acidtypes, such as resins formed by cross-linking polystyrene withdivinylbenzene and sulfonating the cross-linked product. Such resins areillustrated by the structural formula:

| O so,r-1

There are numerous commercial cation exchange resins of this type,including Amberlite IR 112H+, Amberilte 1R -H+ (both are manufactured byRohm and Haas 00.), Dowex 5O W-X8 (manufactured by the Dow 1? 03112 POQHZ Illustrative of a commercially available resin of this type isBio-Rex 63 (manufactured by Bio-Rad Laboratories).

Satisfactory weak cation exchange resins include carboxylic acid types,such as resins formed by copolymerizing metha-crylic acid with across-linking agent, for example divinylbenzene. Such resins areillustrated by the structural formula:

Illustrative of a commercially available resin of this type is AmberliteCG SO-type 1 (manufactured by Rohm and Haas Co.), which is described asa synthetic weakly acidic cation exchange resin; carboxylic acid type;hydrogen form.

Another type of weak cation exchange resin compre-- hends resins havingan --OH group as the ion functional group and formed by reactingpolyhydric phenols with formaldehyde. Such resins are illustrated by thestructural formula:

(H12 011 on OH on -orr oHi oH on? Cm 0132- (EH3 Hg 11 HO-- OH OH OH CHz-CH1- OH OH (|)H I H2 Such resins may be further modified by the additionof one or more additional functional groups. For example, the abovephenol-formaldehyde resin may be sulfonated to introduce sulfonicgroups, giving a resin having both SO H and OH groups, as illustrated inthe structural formula:

OH (3H OH CHg- CHz CH CHg Other variations of the cationic exchangeresins may also be employed. For example, suitable resins includecarbonaceous cation exchange resins of the sulfonated coal-type, ineither the hydrogen or sodium condition, i.e. in which the ion which isreplaced by the nicotine is either hydrogen or sodium. Such resins arecommercially obtainable as, for example Zeo-Karb resins. Another type ofresin which is suitable is the Zeolite type, either natural orsynthetic. These resins are hydrated alkali-aluminum silicates.

The nicotine-resin can be applied to the filter in many different ways.For example, it can be used directly as it is taken from the reactionvessel after its preparation,

or it can first be ground to form smaller particles. The resin particlesize can vary widely. The nicotine-resin particles can be admixed with asticker, such as a corn syrup solution, honey, molasses or other similarmaterial, and can then be sprayed on, admixed with the components of thefilter or otherwise applied to the filter.

The amount of nicotine-resin that is added to the filter will varydepending upon the nicotine content originally present in the tobaccoand upon the nicotine content desired in the tobacco. Generally, thenicotine content of the filter is brought to a level whereby there are0.1-3.0 mg. of nicotine in the smoke per cigarette.

One method of determining how much of a particular nicotine resin to addto a particular filter is to analyze the smoke for nicotine, which canbe done by conventional methods, such as is described in the Journal ofthe Association of Official Agricultural Chemists (vol. 42) (Nov. 2,1959) on pages 424-429. In accordance with this method an aqueoussolution of smoke particulate phase is steam distilled under appropriateconditions; this is followed by spectrophotometric examination of theresulting distillate in the ultraviolet spectral region.

The directions for the details of this procedure include the following:

Collect the smoke particulate phase from 10 successive cigarettes, usinga standard robot smoking procedure (35 (ml. puff volume taken over a 2second interval, once per minute) upon a glass wool plug or anequivalent collection medium suitable for the separation of 0.1particles and larger from a gas particulate phase mixture. Strip thenicotine alkaloids from the collection medium with four 10 ml. portionsof 0.05 N HCl. Combine the separate eluates and dilute to exactly 50 ml.with 0.05 N HCl. Transfer a 10 ml. aliquot of this solution to the portof the distillation unit. Distill approximately 100 ml., and discard.Make the sample in the unit alkaline by adding a size 00 capsule of NaCland a size 00 capsule of NaOH, in that order. Repeat the distillationand collect a second100 ml. portion, as follows: distill approximately98 ml. into a 100 ml. volumetric flask to which 5 ml. 3 N H haspreviously been added. Dilute the distillate exactly to mark withdistilled water, mix well, and examine spectrophotometrically between230 and 300 mg. Correct the absorbance of the unknown solution atapproximately 260 mg by a baseline selected on the basis of the curve.Draw a line from the lowest point on both sides of the maximumabsorbance. The difference between the baseline and peak at the wavelength of the peak is taken as the absorbance of the sample. Comparethis corrected absorbance to the absorbance of the standard nicotinesolution corrected in the same manner, and calculate the nicotinecontent of the sample directly from this comparison, using standardspectrophotometric technique.

Mg nicotine alkaloid=(A/A') (mg. known per ml. dilution factor/no.cigarettes in sample): where A is corrected absorbance of unknown, and Ais corrected absorbance of known. The nicotine-resin content for'thefilter can then be adjusted to bring the nicotine in the smoke to withinthe range which is desired.

In the case of a flavorant, the additive-ion exchange resin can be aflavorant-anion exchange resin, a flavorantinterrnediate ion exchangeresin or a flavorant-cation exchange resin.

Flavorants which can be used in accordance with this invention includeboth acidic and basic flavor materials which will volatilize and bereleased from the ionexchange resin to be carried in the smoke when thetobacco containing the flavorant-ion exchange resin is burned. Basicflavor materials which can-be employed include flavorful alkaloids,amines, myosmine, or qui nine derivatives. For example, the basicflavorants can be: alkaloids, such as nornicotine, cotinene, myosmine,nicotelline, nicotyrine, anabasine, anatabine, and metanicotirie;hetero-cyclic bases, such as pyridine, pyrollidine,

2,3 -dipyridyl, 2-picoline, 3-picoline, 4-picoline, alphacollidine,beta-collidine, gamma-collidine, 2,4-lutidine, 3, 4-lutidine,2,6-lutidine; 3-pyridyl ethyl ketone, 3-pyridyl methyl ketone, methylnicotinate, methyl isonicotinate, 6-methylquinoline, and6-isopropylquinoline; aliphatic amines such as ammonia, triethyla-minebenzylamine, octylamine; aromatic amines such as 3-phenyl-2-propen-l-ylanthranilate, methyl Z-methylaminobenzoate, ethyl oarninobenzoate,methyl anthranilate (methyl o-aminobenzoate) and phenylethylo-aminobenzoate; Schitf bases such as methylN-3,7-dimethyl-7-hydroxyoctylidene-anthranilate and methylN-(p-tert-butyl-alpha-methylhydrocinnamylidene)anthranilate; and aminoacids, such as g'lycine, alanine, glutamine, lysine, valine, leucine,isoleucine, proline, ornithine, arginine, and serine. The preferredbasic flavorants are: nornicotine, myosmine, 3-pyridyl methyl ketone,methyl nicotinate, ethyl o-aminobenzoate, methyl anthranilate (methylo-aminobenzoate), glycine, and alanine. Acidic flavorant materials whichcan be employed include organic carboxylic acids having from 3 to 8carbon atoms, inclusive. Representative acids are the saturatedaliphatic fatty acids, for example propionic acid, n-butyric, andisobutyric acid, 4-methyl valeric acid, 3-anethyl valeric acid,2,2-dimethyl butyric acid, 2-methyl isovaleric acid, straight orbranched chain caprylic acids; the unsaturated fatty acids, such asacrylic acid, crotonic acid, vinylacetic acid, 4-methyl-4-heneoic acid,and methylsorbic acid; the cycloalkane or cycloalkene aliphatic acids,such as cyclopentanecarboxylic acid, cyclohexaneoarboxylic acid,cyclopentaneacetic acid or cyclohexaneacetic acid or the correspondingunsaturated cycloalkenes; the aromatic carboxylic acids, such as benzoicor toluic acids; and phenylacetic acid. In addition the volatilederivatives of the above acids, for example hydroxy acids or keto acidsmay be employed. It is preferred that that flavoring acid be analiphatic or alicyclic saturated monocarboxylic acid of the fatty acidseries having 4, 5, or 6 carbon atoms. 7

Although many of the materials mentioned above either are odorless orhave a disagreeable odor per se when they are smelled in certainconcentrations, they increase the flavor of tobacco smoke when used inlow concentrations by altering the acid-base ratio in the smoke. Theacids also tend to produce a mildness effect.

Cation exchange resins which may be employed with the flavorants, inaccordance with this invention may be strong, weak or intermediatecation exchange resins of the same types as have been described abovewith regard to the nicotine-cation exchange resins.

Anion exchange resins which may be employed in accordance with thisinvention may be strongly basic resins such as the polystyrenequaternary ammonium resins. Satisfactory commercial resins of this typeare Amberlite IRA 400, Amberlite IRA 401, Amberlite IRA 410, Dowex I andDowex 2 and can be illustrated by the formula given below:

Resin obtained by treatment with trimethylamine.

Representing strongly basic anion exchange resins.

Satisfactory Weakly basic anion exchange resins include the primary,secondary, and tertiary amines and are illus- ('3 tratedv by suchcommercially available tertiaryarnines a Amberlite IR 45, Dowex 3;Amberlite IR 4B, Duolite AZ Duolite A4, Duolite A6 and Duolite A7.

Duolite A114, which is representative of the weakl basic anion exchangeresins can be represented by th formula:

CH "H. ?II on ;HZN(CHQ)2HGI Qauommror Resin obtained by treatment withdimethylamine.

The flavorant-ion exchange resin, i.e. the resinate, ca be prepared bycontacting the resin with the fiavor-prodm ing material under eithercontinuous or batch condition: The amount of materials, the temperature,and the time c operation will depend upon the reactants involved. Igeneral, however, the time will be between about 1 secon and about 30minutes and the temperature will be betwee. about 50 and about F. Ionexchange particles i the 2040 mesh size are preferred. At the end of threaction period, the solution can be decanted and th suspended resinateremoved by filtration. The resinat can then be rinsed and air-dried.

Representative equations for the reactions involve in the preparation ofthe flavorant-ion exchange resin ar schematically shown below:

RH RQN R-[R NH]+ Cation-exchange Basic Flavorant-ion resin flavorantexchange resin Acidic FIavorant-ion flavorant exchange resin The filterbase can comprise any filter material whicl is an adsorbent and/orabsorbent material, including th commercially available filtermaterials. For example it can be paper, cellulose acetate, cellulosepaper or syn thetic polymers, such as polyethylene. The filter can alsicontain additives, such as carbon, molecular sieves, crys tallinecellulose, alumina, fullers earth, rice starch, cellu lose powder anddiatomaceous earth.

- The additive-ion exchange resin (resinate) can be adde to the filterbase in a variety of ways. For example, th resinate can be placedbetween the two sections of a dua cellulose acetate filter; a finelydivided resinate can b dispersed in a solvent and sprayed on celluloseacetati tow which is then dried and made into a filter; the I'CSlIlElttcan be ground and added as dust to the cellulose acetate after which thecellulose acetate is made into a filter or the resinates can be made insitu in ion exchange pape or in certain celluloses having ion exchangeactlvity, am the materials are then processed as filters.

The range of levels for application of the resinates i approximately0.01-50 mg./cigt. for all of the additive ion exchange resins on thefilter base. The preferret range is one which will produce 0.10-0.50mg./cigt. o .the flavorant in the smoke.

, The flavorant-ion exchange resin will not decompos under ordinarystorage conditions and does not impar undesirable odors to the tobaccoproduct.

When fibers containing the flavorant-ion exchange resil are attached toa filler rod and smoked, the fiavoran transfers well into the smoke.

The invent on may be illustrated by the following ex amplesAnion-exchange resin Example 1 A sulfonated polystyrene cation exchangeresin (Rohm and Haas Amberlite IR 112) was converted to the PH form andmixed with an aqueous solution of nicotine. After the rapid absorptionof the nicotine was complete, the resin was filtered off and dried inair. Analysis of the dried resin showed that it contained 33%, byweight, of nicotine. It had no detectable odor of nicotine. The percentof nicotine in the resinate did not change signficantly after storingfor one year.

The resin was ground to 60-80 mesh size and incorporated into the filterof dual filter-type cigarettes by placing it between the carbon filterand the cellulose acetate fitler. The amount applied was 20 mg. of theresin per cigarette. A smoking panel, which evaluated the cigarettessubjectively, reported that these cigarettes had the characteristicefifect of nicotine; i.e., they increased throat impact and increasedoverall flavor and smoke sensation as compared with control cigarettesof the same type but containing no resin. Determination of nicotine insmoke by the procedure described earlier in this specification 1 showedthat the cigarettes containing the resin in the filter delivered 0.98mg. per cigarette compared with 0.83 for the control cigarettes.

Example 2 A cation exchange resin of the phosphonic acid type (Bio-Rex63) in the H+ form was treated with nicotine as in Example 1. The resin,after drying contained 30% by weight nicotine. It had no odor ofnicotine. The resin was incorporated into the filter of dual filtercigarettes by the procedure used in Example 1. The increased nicotineefi'ect in the smoke as compared with that of the control was observedsubstantially. The analyses were: resin cigarette 0.96 mg. percigarette, control 0.83 mg. per cigarette nicotine in smoke.

Example 3 The IR 112 resin containing 33% nicotine (Example 1) wasground to pass 200 mesh and then dispersed in ethanol. The ethanolsuspension of the resin was sprayed onto cellulose acetate filter tow.The tow, after spraying was manufactured into filter rods, which werecut into 15 mm. lengths and attached to 57 mm. sections of tobaccofiller to form cigarettes. The amount of resin incorporated into thefilter was 18 mg. per cigarette. These cigarettes, when smoked, had anoticeable nicotine effect when compared with control filter cigarettesmade the same way but containing no resin.

Example 4 1 Journal of the Association of Officlal Agricultural Chemists(vol. 42) (Nov. 2, 1959) on pages 424-429.

dual filter type cigarettes as in Example 1. Fifty mg. per cigarette ofthe resin were applied. These cigarettes were smoked mechanically andthe total particulate material, collected on FTC filters, was analyzedfor glycolic acid by a gas chromatographic procedure. The results were:

Cigarettes with glycolic acid resin in filter: 376 ,wg. of glycolic acidper cigarette glycolic acid.

Control cigarettes with no resin in filter: glycolic acid, less than thedetectable limit of ,ag. per cigarette.

Example 5 A weakly basic tertiary amine type anion exchange resin (Rohm& Haas IRC 45) was converted to the OH" form and was treated with anaqueous solution of acetic acid. After absorption of the acid by theresin was complete, the resin was dried and ground to 60-80 mesh.Analysis of the resin by the same method used in Example 4 showed thatthis resin contained 16.4% acetic acid by weight.

This resin was incorporated into dual filter cigarettes by the methodused in Example 1, at a level of 50 mg. per cigarette. The pH of themainstream smoke from these cigarettes was 5.4; while the pH of controlcigarettes, not containing the resin in the filter gave a mainstreamsmoke pH of 5.9. Analysis of the acetic acid in smoke of thesecigarettes gave the following results:

Cigarettes containing acetic acid-resin in filter: 720 g. acetic acidper cigarette.

Control cigarettes without resin: 460 g. acetic acid per cigarette.

We claim:

A tobacco product comprising a tobacco section and a filter section,said filter section including, prior to ignition of said tobaccosection, a nicotine-ion exchange resin as an integral part thereof, saidnicotine-ion exchange resin being adapted to release nicotine uponcontact with tobacco smoke subsequent to ignition of said tobaccosection, said tobacco section, prior to the ignition of said tobaccosection, being substantially free of said nicotineion exchange resin andhaving a nicotine content which is below that of a conventional tobaccoproduct, whereby smoke produced by ignition of said tobacco sectionpassing from said tobacco section through said filter section andemerging from said filter section, will have a nicotine contentapproximating that of a conventional tobacco product.

References Cited by the Examiner UNITED STATES PATENTS 2,293,954 8/ 1942Tiger 131208 2,739,598 5/1956 Eirich 131l0 2,754,829 7/1956 Hess 131-2082,839,065 6/1958 Milton 131-10 3,047,431 7/1962 Bavley et a1. 131173,109,436 11/1963 Bavley 131-17 FOREIGN PATENTS 173,262 12/ 1952Austria.

OTHER REFERENCES Linde: Chemical-Loaded Molecular Sieves, Form F- 1311,published by Linde Co., Division of Union Carbide Corp., Aug. 3, 1959.

SAMUEL KOREN, Primary Examiner.

M. D. REIN, Examiner.

